Pyrazine-diium bis-(3-carb-oxy-4-hydroxy-benzene-sulfonate) dihydrate.

Pyrazine and 5-sulfosalicylic acid crystallize from a methanol solution containing water as the title salt, C(4)H(6)N(2) (2+)·2C(7)H(5)O(6)S(-)·2H(2)O. The pyrazine-diium cation sits on an inversion center. The component ions and water mol-ecules are linked by inter-molecular O-H⋯O, N-H⋯O and C-H⋯O hydrogen bonds into layers running parallel to the (10) plane.

Related literature

For related literature, see: Smith et al. (2004 ▶, 2005 ▶); Meng et al. (2008 ▶).

Experimental

Crystal data

C4H6N2 2+·2C7H5O6S−·2H2O

M = 552.48

Triclinic,

a = 6.7887 (5) Å

b = 6.9256 (6) Å

c = 13.0349 (10) Å

α = 100.663 (7)°

β = 97.761 (9)°

γ = 107.735 (9)°

V = 561.52 (9) Å3

Z = 1

Mo Kα radiation

μ = 0.32 mm−1

T = 298 (2) K

0.20 × 0.10 × 0.08 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1997 ▶) T min = 0.929, T max = 0.975

5286 measured reflections

2412 independent reflections

1977 reflections with I > 2σ(I)

R int = 0.064

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.131

S = 1.08

2412 reflections

178 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.32 e Å−3

Δρmin = −0.51 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SMART; data reduction: SAINT-Plus (Bruker, 2001 ▶; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808017777/cs2079sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808017777/cs2079Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C4H6N22+·2C7H5O6S–·2H2O	Z = 1
Mr = 552.48	F000 = 286
Triclinic, P1	Dx = 1.634 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 6.7887 (5) Å	Cell parameters from 2269 reflections
b = 6.9256 (6) Å	θ = 1.6–25.2º
c = 13.0349 (10) Å	µ = 0.32 mm−1
α = 100.663 (7)º	T = 298 (2) K
β = 97.761 (9)º	Plate, colourless
γ = 107.735 (9)º	0.20 × 0.10 × 0.08 mm
V = 561.52 (9) Å3

Bruker SMART APEX CCD area-detector diffractometer	2412 independent reflections
Radiation source: fine focus sealed Siemens Mo tube	1977 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.064
T = 298(2) K	θmax = 27.0º
0.3° wide ω exposures scans	θmin = 1.6º
Absorption correction: multi-scan(SADABS; Sheldrick, 1997)	h = −8→8
Tmin = 0.929, Tmax = 0.975	k = −5→8
5286 measured reflections	l = −16→16

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.131	w = 1/[σ2(Fo2) + (0.0732P)2 + 0.0236P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max = 0.001
2412 reflections	Δρmax = 0.32 e Å−3
178 parameters	Δρmin = −0.51 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

	x	y	z	Uiso*/Ueq
C1	0.4240 (3)	0.7285 (3)	0.48381 (14)	0.0311 (4)
C2	0.6433 (3)	0.7939 (3)	0.48820 (17)	0.0361 (5)
C3	0.7816 (3)	0.8439 (3)	0.58633 (18)	0.0439 (5)
H3	0.9265	0.8851	0.5895	0.053*
C4	0.7052 (3)	0.8328 (3)	0.67817 (17)	0.0425 (5)
H4	0.7985	0.8671	0.7432	0.051*
C5	0.4881 (3)	0.7704 (3)	0.67421 (15)	0.0338 (4)
C6	0.3486 (3)	0.7183 (3)	0.57800 (14)	0.0323 (4)
H6	0.2040	0.6762	0.5758	0.039*
C7	0.2761 (3)	0.6708 (3)	0.38006 (15)	0.0362 (5)
C8	0.9086 (4)	0.6243 (4)	0.96127 (19)	0.0543 (6)
H8	0.8459	0.7119	0.9346	0.065*
C9	0.8819 (4)	0.3018 (4)	0.99291 (18)	0.0511 (6)
H9	0.8012	0.1641	0.9884	0.061*
N1	0.7935 (3)	0.4275 (3)	0.95466 (13)	0.0466 (5)
H1B	0.658 (4)	0.377 (4)	0.928 (2)	0.056*
O1	0.0776 (2)	0.6158 (3)	0.38832 (11)	0.0484 (4)
H1A	−0.005 (5)	0.578 (5)	0.331 (2)	0.073*
O2	0.3328 (3)	0.6740 (3)	0.29528 (11)	0.0531 (4)
O3	0.7255 (3)	0.8128 (3)	0.40112 (14)	0.0523 (4)
H3A	0.633 (5)	0.788 (5)	0.348 (3)	0.078*
O4	0.2517 (3)	0.8910 (3)	0.79365 (12)	0.0535 (4)
O5	0.2546 (2)	0.5428 (2)	0.78053 (11)	0.0467 (4)
O6	0.5615 (3)	0.8329 (3)	0.88036 (11)	0.0522 (4)
O7	0.3909 (3)	0.2940 (3)	0.88232 (12)	0.0475 (4)
H7A	0.346 (5)	0.362 (5)	0.844 (2)	0.071*
H7B	0.340 (5)	0.169 (5)	0.849 (2)	0.071*
S1	0.38501 (8)	0.76139 (8)	0.79128 (3)	0.0378 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0308 (9)	0.0259 (10)	0.0391 (9)	0.0108 (8)	0.0074 (8)	0.0115 (8)
C2	0.0321 (10)	0.0272 (10)	0.0533 (11)	0.0111 (8)	0.0152 (8)	0.0130 (9)
C3	0.0247 (10)	0.0414 (12)	0.0655 (13)	0.0105 (9)	0.0075 (9)	0.0150 (10)
C4	0.0325 (10)	0.0412 (12)	0.0495 (11)	0.0106 (9)	−0.0022 (9)	0.0113 (9)
C5	0.0319 (10)	0.0293 (10)	0.0391 (9)	0.0103 (8)	0.0030 (8)	0.0090 (8)
C6	0.0265 (9)	0.0316 (11)	0.0391 (9)	0.0101 (8)	0.0044 (7)	0.0103 (8)
C7	0.0369 (11)	0.0349 (11)	0.0396 (10)	0.0125 (9)	0.0085 (8)	0.0145 (8)
C8	0.0648 (16)	0.0550 (16)	0.0518 (13)	0.0315 (13)	0.0084 (11)	0.0173 (11)
C9	0.0617 (15)	0.0454 (14)	0.0481 (12)	0.0214 (12)	0.0105 (11)	0.0113 (10)
N1	0.0443 (10)	0.0565 (13)	0.0383 (9)	0.0203 (10)	0.0045 (8)	0.0073 (9)
O1	0.0322 (8)	0.0695 (12)	0.0376 (7)	0.0083 (8)	0.0005 (6)	0.0184 (7)
O2	0.0521 (9)	0.0701 (12)	0.0390 (8)	0.0189 (9)	0.0136 (7)	0.0176 (7)
O3	0.0404 (9)	0.0604 (11)	0.0606 (10)	0.0151 (8)	0.0235 (7)	0.0190 (8)
O4	0.0572 (10)	0.0634 (11)	0.0488 (8)	0.0343 (9)	0.0092 (7)	0.0126 (7)
O5	0.0447 (9)	0.0477 (10)	0.0400 (7)	0.0053 (7)	0.0014 (6)	0.0148 (7)
O6	0.0515 (9)	0.0557 (10)	0.0383 (7)	0.0133 (8)	−0.0093 (7)	0.0064 (7)
O7	0.0571 (10)	0.0444 (10)	0.0467 (8)	0.0238 (8)	0.0082 (7)	0.0152 (7)
S1	0.0369 (3)	0.0405 (3)	0.0328 (3)	0.0128 (2)	−0.0006 (2)	0.0074 (2)

C1—C6	1.398 (3)	C8—N1	1.329 (3)
C1—C2	1.408 (3)	C8—C9i	1.363 (4)
C1—C7	1.478 (2)	C8—H8	0.9300
C2—O3	1.341 (3)	C9—N1	1.329 (3)
C2—C3	1.397 (3)	C9—C8i	1.363 (4)
C3—C4	1.373 (3)	C9—H9	0.9300
C3—H3	0.9300	N1—H1B	0.87 (3)
C4—C5	1.395 (3)	O1—H1A	0.82 (3)
C4—H4	0.9300	O3—H3A	0.83 (3)
C5—C6	1.380 (2)	O4—S1	1.4556 (17)
C5—S1	1.766 (2)	O5—S1	1.4721 (15)
C6—H6	0.9300	O6—S1	1.4421 (14)
C7—O2	1.220 (2)	O7—H7A	0.83 (3)
C7—O1	1.310 (2)	O7—H7B	0.83 (3)
C6—C1—C2	119.40 (17)	O1—C7—C1	113.11 (16)
C6—C1—C7	120.76 (17)	N1—C8—C9i	120.2 (2)
C2—C1—C7	119.84 (17)	N1—C8—H8	119.9
O3—C2—C3	118.37 (18)	C9i—C8—H8	119.9
O3—C2—C1	122.21 (19)	N1—C9—C8i	119.6 (2)
C3—C2—C1	119.41 (18)	N1—C9—H9	120.2
C4—C3—C2	120.51 (19)	C8i—C9—H9	120.2
C4—C3—H3	119.7	C8—N1—C9	120.2 (2)
C2—C3—H3	119.7	C8—N1—H1B	122.3 (17)
C3—C4—C5	120.19 (19)	C9—N1—H1B	117.4 (18)
C3—C4—H4	119.9	C7—O1—H1A	113 (2)
C5—C4—H4	119.9	C2—O3—H3A	111 (2)
C6—C5—C4	120.25 (18)	H7A—O7—H7B	107 (3)
C6—C5—S1	118.43 (15)	O6—S1—O4	114.02 (10)
C4—C5—S1	121.30 (15)	O6—S1—O5	111.78 (9)
C5—C6—C1	120.23 (17)	O4—S1—O5	109.60 (10)
C5—C6—H6	119.9	O6—S1—C5	107.54 (10)
C1—C6—H6	119.9	O4—S1—C5	106.61 (9)
O2—C7—O1	123.31 (18)	O5—S1—C5	106.90 (9)
O2—C7—C1	123.58 (18)
C6—C1—C2—O3	−177.99 (18)	C6—C1—C7—O2	−179.0 (2)
C7—C1—C2—O3	2.2 (3)	C2—C1—C7—O2	0.8 (3)
C6—C1—C2—C3	1.1 (3)	C6—C1—C7—O1	1.0 (3)
C7—C1—C2—C3	−178.71 (18)	C2—C1—C7—O1	−179.17 (18)
O3—C2—C3—C4	178.12 (19)	C9i—C8—N1—C9	0.2 (4)
C1—C2—C3—C4	−1.0 (3)	C8i—C9—N1—C8	−0.2 (4)
C2—C3—C4—C5	0.3 (3)	C6—C5—S1—O6	−176.94 (15)
C3—C4—C5—C6	0.3 (3)	C4—C5—S1—O6	1.7 (2)
C3—C4—C5—S1	−178.24 (16)	C6—C5—S1—O4	−54.28 (18)
C4—C5—C6—C1	−0.2 (3)	C4—C5—S1—O4	124.33 (19)
S1—C5—C6—C1	178.39 (14)	C6—C5—S1—O5	62.88 (17)
C2—C1—C6—C5	−0.5 (3)	C4—C5—S1—O5	−118.51 (18)
C7—C1—C6—C5	179.32 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O6	0.93	2.40	3.273 (3)	156
C9—H9···O6ii	0.93	2.41	3.240 (3)	149
C6—H6···O1iii	0.93	2.49	3.249 (2)	139
N1—H1B···O7	0.87 (3)	1.71 (3)	2.580 (3)	176 (3)
O7—H7A···O5	0.83 (3)	1.84 (3)	2.659 (2)	171 (3)
O7—H7B···O4ii	0.83 (3)	1.81 (3)	2.631 (3)	172 (3)
O3—H3A···O2	0.83 (3)	1.92 (3)	2.625 (2)	143 (3)
O1—H1A···O5iii	0.82 (3)	1.92 (3)	2.719 (2)	163 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯O6	0.93	2.40	3.273 (3)	156
C9—H9⋯O6i	0.93	2.41	3.240 (3)	149
C6—H6⋯O1ii	0.93	2.49	3.249 (2)	139
N1—H1B⋯O7	0.87 (3)	1.71 (3)	2.580 (3)	176 (3)
O7—H7A⋯O5	0.83 (3)	1.84 (3)	2.659 (2)	171 (3)
O7—H7B⋯O4i	0.83 (3)	1.81 (3)	2.631 (3)	172 (3)
O3—H3A⋯O2	0.83 (3)	1.92 (3)	2.625 (2)	143 (3)
O1—H1A⋯O5ii	0.82 (3)	1.92 (3)	2.719 (2)	163 (3)

Symmetry codes: (i) ; (ii) .